Water → Ethyl(6-(((trifluoromethyl)sulfonyl)oxy)-1-benzothiophen-3-yl)acetate

HRID 591486Notes

Reaction equation

HRID 591486 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:9]=2[S:8][CH:7]=1)[CH3:2].C(N(CC)CC)C.[O:24](S(C(F)(F)F)(=O)=O)[S:25]([C:28]([F:31])([F:30])[F:29])(=O)=[O:26].O>CC#N>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][S:25]([C:28]([F:31])([F:30])[F:29])(=[O:26])=[O:24])=[CH:14][C:9]=2[S:8][CH:7]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 57431998(6-Hydroxy-benzo[b]thiophen-3-yl)-acetic acid ethyl ester

Product 1

HCID 57443344Ethyl(6-(((trifluoromethyl)sulfonyl)oxy)-1-benzothiophen-3-yl)acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl(6-hydroxy-1-benzothiophen-3-yl)acetate (500 mg) and triethylamine (0.592 mL) in CH3CN (20 mL) was added Tf2O (0.417 mL). The mixture was stirred at 0° C. for 10 min. The mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, washed successively with 1N HCl and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (745 mg).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed successively with 1N HCl and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-99f88f73cddc45bbbfdbc950a2b3a946
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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